US 11,672,173 B2
Organic light-emitting device
Seulong Kim, Yongin-si (KR); Younsun Kim, Yongin-si (KR); Dongwoo Shin, Yongin-si (KR); Jungsub Lee, Yongin-si (KR); Naoyuki Ito, Yongin-si (KR); and Jino Lim, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Nov. 18, 2021, as Appl. No. 17/530,403.
Application 17/530,403 is a continuation of application No. 15/965,772, filed on Apr. 27, 2018, granted, now 11,211,564.
Application 15/965,772 is a continuation of application No. 15/242,040, filed on Aug. 19, 2016, granted, now 9,960,361, issued on May 1, 2018.
Claims priority of application No. 10-2015-0118277 (KR), filed on Aug. 21, 2015; and application No. 10-2016-0104281 (KR), filed on Aug. 17, 2016.
Prior Publication US 2022/0077399 A1, Mar. 10, 2022
Int. Cl. H01L 51/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H01L 51/50 (2006.01); H01L 51/52 (2006.01)
CPC H01L 51/0061 (2013.01) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H01L 51/006 (2013.01); H01L 51/0067 (2013.01); H01L 51/0071 (2013.01); H01L 51/0072 (2013.01); H01L 51/0073 (2013.01); H01L 51/0085 (2013.01); H01L 51/5056 (2013.01); H01L 51/5072 (2013.01); H01L 51/5088 (2013.01); H01L 51/5092 (2013.01); H01L 51/52 (2013.01); H01L 51/5271 (2013.01); C09K 2211/185 (2013.01); H01L 51/0052 (2013.01); H01L 51/0054 (2013.01); H01L 51/0058 (2013.01); H01L 51/5012 (2013.01)] 20 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
a first layer between the first electrode and the second electrode, the first layer comprising a first compound;
a second layer between the first layer and the second electrode, the second layer comprising a second compound; and
a third layer between the second layer and the second electrode, the third layer comprising a third compound;
wherein the first compound does not comprise a nitrogen-containing heterocyclic group comprising *═N—*′ as a ring forming moiety, and
wherein the first compound is selected from compounds represented by Formulae 1-1 to 1-3, Formulae 2H-1, 2D-1, 2D-2, Formulae 3-1 and 3-2, the second compound is selected from compounds represented by Formulae 1-1 to 1-3, Formulae 2D-1 and 2D-2, and the third compound is selected from compounds represented by Formulae 2H-1, 2D-1, 2D-2, Formulae 3-1 and 3-2:

OG Complex Work Unit Chemistry
wherein, in Formulae 1-1, 1-2, 1-3, 2H-1, 2D-1, 2D-2, 3-1, and 3-2,
X1 is C(R41) or N,
X2 is C(R42) or N,
X3 is C(R43) or N,
L21 to L24, L31 to L34, and L41 to L43 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
L25 is selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 non-condensed arylene group, and a substituted or unsubstituted C1-C60 non-condensed heteroarylene group,
L35 is selected from a substituted or unsubstituted C6-C60 condensed polycyclic arylene group, a substituted or unsubstituted C1-C60 condensed polycyclic heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
b1 to b5, d1 to d5, and g1 to g3 are each independently an integer selected from 0 to 3,
Ar21 to Ar24, Ar31 to Ar34, and Ar41 to Ar43 are each independently a group selected from groups represented by Formulae A to C, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a biphenyl group, a terphenyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R21 to R24, R31, and R41 to R44 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, and —Si(Q43)(Q44)(Q45),
c1, c4, h1, and h4 are each independently an integer selected from 0 to 4, e1 is an integer selected from 0 to 4, and c2, c3, h2, and h3 are each independently an integer selected from 0 to 3,
in Formula 1-1, at least one selected from Ar21 to Ar23 is a group selected from groups represented by Formulae A to C,
in Formula 1-2, at least one selected from Ar21 to Ar24 is a group selected from groups represented by Formulae A to C,
in Formula 1-3, at least one selected from Ar21 and Ar22 is a group selected from groups represented by Formulae A to C,
in Formula 2H-1, Ar31 is a group selected from groups represented by Formulae A to C,
in Formula 2D-1, at least one selected from Ar31 to Ar34 is a group selected from groups represented by Formulae A to C,
in Formula 2D-2, at least one selected from Ar31 to Ar33 is a group selected from groups represented by Formulae A to C, wherein the group selected from groups represented by Formulae A to C comprises —N(Q1)(Q2),
in Formula 3-1, at least one selected from Ar41 to Ar43 is a group selected from groups represented by Formulae A to C,
in Formula 3-2, one selected from Ar41 and Ar42 is a group selected from groups represented by Formulae A to C, and
at least one substituent of the substituted C3-C10 cycloalkylene group, substituted C1-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C1-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C6-C60 non-condensed arylene group, substituted C6-C60 condensed polycyclic arylene group, substituted C1-C60 heteroarylene group, substituted C1-C60 non-condensed heteroarylene group, substituted C1-C60 condensed polycyclic heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C1-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q13)(Q14)(Q15);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, and —Si(Q23)(Q24)(Q25); and
—Si(Q33)(Q34)(Q35),
wherein Q13 to Q15, Q23 to Q25, Q33 to Q35, and Q43 to Q45 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,
wherein the first compound, the second compound, and the third compound each independently comprise at least one group selected from groups represented by Formulae A to C:

OG Complex Work Unit Chemistry
wherein, in Formulae A to C,
ring A1, ring A11, and ring A12 are each independently selected from a C5-C30 carbocyclic group and a C2-C30 heterocyclic group,
R1, R2, R11, and R12 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7),
wherein Q1 to Q7 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
a1, a11, and a12 are each independently an integer selected from 0 to 10,
a2 is an integer selected from 0 to 2,
wherein * and *′ each indicate a binding site to an adjacent atom.